Fresh Pineapple Upside Down Cake

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This Ultimate Fresh Pineapple Upside Down Cake has caramelized fresh pineapple basking in a rich butter brown sugar gooiness atop a fluffy vanilla cake.  So much caramelized yumminess, it’s insane.

Perfect for Mother’s Day and summer dessert deliciousness! You may want to check out this Pineapple Coconut Banana Bread and this Heavenly Hash Pineapple Fluff Dessert too!

Fresh Pineapple Upside Down Cake recipe homemade

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How Did Upside Down Cakes Come About?

Developed centuries ago, this Classic Pineapple Cake has stood the test of time. These kinds of cakes used to be cooked in cast iron skillets over an open fire. Then, fruit and sugar was added to the bottom of the skillet and cake batter was poured over the mixture.

Once cooked, flipping it over onto a plate not only released the cake from the skillet, but showed how pretty the caramelized fruit was on top.  Ta-dahhhh!

Fresh Pineapple Upside Down Cake recipe homemade

Why We Love This Fresh Pineapple Upside Down Cake!

  • I LOVE the Classic Desserts!  That’s why this awesome pineapple cake deserves to be put on a pedestal.
  • Got fresh pineapple? How can we resist it in this upside down cake recipe!
  • The caramelization of the pineapples and brown sugar and butter in the cake is amazing!
  • The hardest part is cutting up the pineapple!  Here’s how, but you can use canned pineapple, but we love the fresh pineapple idea!
  • Perfect summer baking dessert after dinner!
  • Impressive!

Ultimate Fresh Pineapple Upside Down Cake

This delicious upside down dessert consists of a fluffy white vanilla cake made with fresh pineapple, brown sugar and butter for the caramelization.

With this dessert recipe, you basically cook the fruit with the butter and brown sugar until tender and then place it in the bottom of your pan.  Make and dollop the cake batter on top and then smooth out. Bake away! Leave to stand for 5 minutes then turn out onto your platter.

But of course, if you don’t have fresh pineapple, you can absolutely use canned pineapple. I had a fresh pineapple on hand I bought at the grocery (ALDI) and have wanted to make this vintage recipe with them to put on the blog, so here we are.

Finally getting to it.  There’s like a million desserts I want to make, but this is one I definitely wanted to share with you.

Fresh Pineapple Upside Down Cake recipe homemade

Ingredients You Need

Bottom of Cake

  • brown sugar

Caramelized Fresh Pineapple

  • brown sugar
  • unsalted butter 
  • 1 large pineapple—peeled & quartered, cored and sliced ⅓ inch thick (You may want to cut the pineapple up smaller if you want smaller chunks.)

Vanilla Cake

  • unsalted butter 
  • granulated sugar
  • Greek yogurt or sour cream
  • eggs
  • vanilla extract
  • all-purpose flour
  • baking powder
  • baking soda
  • salt

Fresh Pineapple Upside Down Cake recipe homemade

Instructions How to Make Pineapple Upside Down Cake

Pan Preparation

  1. Preheat the oven to 350°.
  2. Butter a deep dish 8-inch or 9-inch round cake pan. Sprinkle the bottom with 2 tablespoons of the brown sugar.

Caramelized Fresh Pineapple

  1. In a large skillet, combine ¾ cup of brown sugar with ½ stick of butter and cook over moderately low heat until the butter is melted. Add the pineapple and cook over moderately low heat, stirring occasionally, about 20 minutes or pineapple is tender. Using a slotted spoon, arrange the slices in the cake pan, overlapping them if necessary, then pour the pan juices over the pineapple, set aside.

Vanilla Cake

  1. In a medium bowl, whisk together the flour, baking powder, baking soda and salt, set aside.
  2. In a large bowl, whisk together yogurt, eggs, vanilla, set aside.
  3. Using mixer, mix together the softened butter and sugar for 2 minutes on medium speed and then add in the yogurt/egg mixture and mix together.
  4. Add flour mixture to the yogurt mixture and mix just until combined and no lumps appear.
  5. Spoon the batter over the pineapple and spread it evenly.
  6. Bake for about 40 minutes, until the cake is deep golden. Let cool for 5 minutes on a rack. Run a knife around the edge of the cake, invert it onto a plate and remove the pan.Replace any pineapple that may have stuck to the pan. Serve warm or at room temperature.

Fresh Pineapple Upside Down Cake recipe homemade

Use Any 8 Inch Baking Pan that isn’t a Springform Pan

  • Lesson learned!  When you make these types of upside down cakes, Once things start heating up, that glorious butter brown sugar glaze is going to drip and spill in your stove and make a huge mess in your oven.  Then you’ll probably be mad at me.  So I’m letting you know it’s best not to use a springform pan if possible. 🙂
  • Bake it in a regular 8″ buttered cake pan to get ultimate results.

Ultimate Fresh Pineapple Upside Down Cake

Serve warm or room temp.  We love fresh whipped cream with cherries with ours, but you could add a yummy scoop of vanilla ice cream and caramel topping, whipped cream and a cherry to delight in the Absolute Ultimate Fresh Pineapple Upside Down Cake treat.

More Cake Classics!  

Ultimate Fresh Pineapple Upside Down Cake

Ultimate Fresh Pineapple Upside Down Cake

Kim Lange
This Ultimate Fresh Pineapple Upside Down Cake has caramelized fresh pineapple basking in a rich butter brown sugar gooiness atop a fluffy vanilla cake and it's INSANE!
3.89 from 34 votes
Prep Time 25 minutes
Cook Time 1 hour
Course Dessert
Servings 12 Slices
Calories 157 kcal

Ingredients
  

Bottom of Cake:

Caramelized Pineapple:

  • ¾ cup brown sugar
  • ½ stick unsalted butter softened
  • 1 large pineapple—peeled quartered, cored and sliced 1/3 inch thick (You may want to cut the pineapple up smaller if you want smaller chunks.)

Vanilla Cake

Instructions
 

  • Pan Preparation:
  • Preheat the oven to 350°.
  • Butter an deep dish 8-inch or 9-inch round cake pan. Sprinkle the bottom with 2 tablespoons of the brown sugar.

Carmelized Pineapple:

  • In a large skillet, combine 3/4 cup of brown sugar with 1/2 stick of butter and cook over moderately low heat until the butter is melted. Add the pineapple and cook over moderately low heat, stirring occasionally, about 20 minutes or pineapple is tender. Using a slotted spoon, arrange the slices in the cake pan, overlapping them if necessary, then pour the pan juices over the pineapple, set aside.

Vanilla Cake:

  • In a medium bowl, whisk together the flour baking powder, baking soda and salt, set aside.
  • In a large bowl, whisk together yogurt, eggs, vanilla, set aside.
    Using mixer, mix together the softened butter and sugar for 2 minutes on medium speed and then add in the yogurt/egg mixture and mix together.
    Add flour mixture to the yogurt mixture and mix just until combined and no lumps appear.
  • Spoon the batter over the pineapple and spread it evenly.
  • Bake for about 40 minutes, until the cake is deep golden. Let cool for 5 minutes on a rack. Run a knife around the edge of the cake, invert it onto a plate and remove the pan.
  • Replace any pineapple that may have stuck to the pan. Serve warm or at room temperature.

Notes

Canned pineapple can be used as well.

Nutrition

Calories: 157kcalCarbohydrates: 38gProtein: 1gFat: 1gSaturated Fat: 1gSodium: 125mgPotassium: 49mgFiber: 1gSugar: 28gCalcium: 22mgIron: 1mg
Keyword cake, pineapple, summer desserts, vanilla cake
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